Simple and Efficient “One‐Pot” Synthesis of Diphenylaryl (Heteroaryl) Methanols from Benzene

Diphenylaryl (heteroaryl) methanols are valuable compounds, widely used in organic synthesis as tailor‐made protective groups, in medicinal chemistry, in crystal engineering, and in many other fields. A simple and efficient “one‐pot” method for the synthesis of diphenylaryl (heteroaryl) methanols fr...

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Veröffentlicht in:ChemistrySelect (Weinheim) 2020-07, Vol.5 (26), p.7835-7839
Hauptverfasser: Akhrem, Irena S., Avetisyan, Dzhul'etta V., Afanas'eva, Lyudmila V., Artyushin, Oleg I.
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Sprache:eng
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Zusammenfassung:Diphenylaryl (heteroaryl) methanols are valuable compounds, widely used in organic synthesis as tailor‐made protective groups, in medicinal chemistry, in crystal engineering, and in many other fields. A simple and efficient “one‐pot” method for the synthesis of diphenylaryl (heteroaryl) methanols from benzene was developed using the known reaction of benzene with CCl4•AlCl3. This approach appeared fruitful when the reaction was performed uring CCl4 as a solvent. This method allows the selective synthesis of Ph2CCl2 in good yield as well as triaryl (heteroaryl) methanols, A simple method for the synthesis of valuable trityl alcohols from benzene and arenes has been developed. It involves reaction of arene or heteroarene with Ph2CCl2 generated from benzene and CCl4⋅AlCl3. Reaction conditions: (1) C6H6+CCl4⋅AlCl3, rt, 1 h; (2) ArH+Ph2CCl2, 0÷60 °C, 0.3–3.0 h. The advantages over the known methods include: easy availability of the starting compounds; no need for inert atmosphere or strictly anhydrous synthesis conditions; simple “one‐pot” procedure; high selectivity; and good to moderate yields of desired products.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201904255